ANR 2015 - JCJC "PORFUSION" - Electrochemically-driven Pi-extension of porphyrins

Pi-extension of porphyrins, i.e. fusion of one or several aromatic hydrocarbon(s) or aromatic heterocycle(s) onto the porphyrin periphery by intramolecular chemical oxidative coupling has attracted much attention because of potential applications in Near-IR electroluminescence displays, photovoltaic solar cells, non-linear optical materials, photodynamic therapy and molecular electronics. However, as mentioned in 2013 by Osuka, “New efficient fusion reactions under milder conditions are highly desirable in future developments”. For this purpose, as reported in 2012 by Gryko, “a better understanding of the mechanism of these intramolecular oxidative couplings is needed, specifically which moiety (porphyrin or the second aromatic system) is first attacked by the oxidant”. 
Thus this project will take advantage of electrochemistry and theoretical calculations to investigate fusion reaction mechanism with unprecedented peripheral aromatic fragments. Besides, this fusion reaction will be performed by electrosynthesis under mild conditions.

Principal Investigator: Dr Charles Devillers